The way I use the question “What if” is to think outside the box and set goals that are crazy. I call it write music that you can't play. Set goals for yourself where you don't know how, but you know what. Don't start with what's possible. Start with: what's cool, what's right.
When you have a goal like this, from my experience of goal setting, three things are going to happen:
#1: When you set this goal, you'll have a completion date, and you probably won't make it. We usually don't make it in time. Why? You've never done it before. This is a new thing. So you're setting out to do something that's not been done and you don't know how long it'll take. Be ready for it to change.
#2: When you get back home and you start to act on your new goal, you will have a plan in the beginning and it will not go according to your plan. You have to have the plan in the beginning but it's going to change. You have to be flexible.
#3: I want you to remember this for the day you get back at work. To do things you have never done, you have to start by doing things you've never done.
One of the boldest goals I ever set for myself was to learn how to play Bohemian Rhapsody on the guitar. It took a lot of work and accepting these three things as they happen.